Abstract
A complex of anthracene with methyl-beta-cyclodextrin (A-Me-β-CD) having fluorophoric characteristics was obtained in aqueous medium. Spectroscopic and thermal analyses of the complex were performed by Fourier transform infrared spectroscopy and differential scanning calorimetry-thermogravimetry. The interaction of Me-β-CD and anthracene was also analyzed by means of spectrometry by a UV–Vis spectrophotometer. The stoichiometry of the complex was determined by the Benesi–Hildebrand method. The complex formation constant was found to be (42 ± 3) × 103 L·mol−1. The Gibbs energy and excited singlet state energy were calculated. The mechanism of the quenching effect of Co(II) and Ni(II) metals in the inclusion complex was studied. The Stern–Volmer constant, bimolecular quenching rate constant, lifetime and approximate activation energy values were determined, and the quenching was found to be diffusion controlled dynamic quenching. In addition, with the energy band calculations made, it was shown by means of Taug curves that electron transfer was made to Ni and Co metals from the complex fluorophore group in the quenching mechanism.
Similar content being viewed by others
References
Anitha, A., Murugan, M., Rajamohan, R.: Molecular encapsulation of amodiaquine in 2-hydroxypropyl β-cyclodextrin cavity. Characterization and its in vitro cytotoxicity. Spectrosc. Lett. 51, 198–204 (2018)
Murugan, M., Anitha, A., Sivakumar, K., Rajamohan, R.: Supramolecular ınteraction of primaquine with native β-cyclodextrin. J. Solution Chem. 47, 906–929 (2018)
Sabari, C.L., Sivakumar, K., Rajamohan, R.: Improvement of cytotoxic activity of local anesthetics against human breast cancer cell line through the cyclodextrin complexes. J. Macromol. Sci. A 54, 402–410 (2017)
Sambasevam, K.P., Mohamad, S., Sarih, N.M., Ismail, N.A.: Synthesis and characterization of the ınclusion complex of β-cyclodextrin and azomethine. Int. J. Mol. Sci. 14, 3671–3682 (2013)
Norkus, E.: Metal ion complexes with native cyclodextrins. An overview. J. Incl. Phenom. Macrocycl. Chem. 65, 237–248 (2009)
Kemtong, C., Banerjee, D., Liu, Y., El Khoury, J.M., Rinaldi, P.L., Hu, J.: Formation of an ınclusion complex of a new transition metal ligand in β-cyclodextrin. Supramol. Chem. 17, 335–341 (2005)
Jullian, C., Brossard, V., Gonzalez, I., Alfaro, M., Olea-Azar, C.: Cyclodextrins-kaempferol ınclusion complexes: spectroscopic and reactivity studies. J. Solution Chem. 40, 727–739 (2011)
Ay, U., Dogruyol, Z., Arsu, N.: The effect of heavy metals on the anthracene-me-β-cyclodextrin host-guest ınclusion complexes. Supramol. Chem. 26, 66–70 (2014)
Ay, U., Sarlı, S.E.: Investigation by fluorescence technique of the quenching effect of Co2+ and Mn2+ transition metals, on naphthalene-methyl-beta-cyclodextrin host-guest ınclusion complex. J. Fluoresc. 28, 1371–1378 (2018)
Morris, J.V., Mahoney, M.A., Huber, J.R.: Fluorescence quantum yield determinations. 9,10-dipenylanthracene as a reference standard in different solvents. J. Phys. Chem. 80, 969–974 (1976)
Balta, D.K., Temel, G., Aydın, M., Arsu, N.: Thioxanthone based water-soluble photoinitiators for acrylamide photopolymerization. Eur. Polym. J. 46, 1374–1379 (2010)
Ozkazanc, E., Ozkazanc, H., Gundogdu, O.: Characterization and charge transport mechanism of multifunctional polyfuran/tin(IV) oxide composite. J. Inorg. Organomet. 28, 2108–2120 (2018)
Kumar, A., Kumar, A., Sharma, G., Al-Muhtaseb, A.H., Naushad, M., Ghfar, A.A., Stadler, F.J.: Quaternary magnetic BiOCl/g-C3N4/Cu2O/Fe3O4 nano-junction for visible light and solar powered degradation of sulfamethoxazole from aqueous environment. Chem. Eng. J. 334, 462–478 (2018)
University of Zurich, Department of Chemistry Home Page. https://www.chem.uzh.ch/de/study/download/year2/che211.html
Baggott, J.E., Pilling, M.J.: Temperature dependence of excited-state electron-transfer reactions quenching of RuL32+ emission by copper(II) and europium(III) in aqueous solution. J. Phys. Chem. 84, 3012–3019 (1980)
Stanculescu, I., Dobrica, I., Mandravel, C., Mindrila, G.: Anal. Univ. Bucuresti-Chimie (serienoua) 19, 47 (2010)
Drössler, P., Holzer, W., Penzkofer, A., Hegemann, P.: Fluoresence quenching of riboflavin in aqueous solution by methionin and cystein. Chem. Phys. 286, 409–420 (2003)
Marzouqi, A.H.A., Shehatta, I., Jobe, B., Dowaidar, A.: Phase solubility and inclusion complex of Itraconazole with ß-cyclodextrin using supercritical carbon dioxide. J. Pharm. Sci. 95, 292–304 (2006)
Jadhav, G.S., Vavia, P.R.: Physicochemical, in silico and in vivo evaluation of a Danazol–β-cyclodextrin complex. Int. J. Pharm. 352, 5–16 (2008)
Chow, D.D., Karara, A.K.: Characterization, dissolution and bioavailabilty in rats of Ibuprofen- β-cyclodextrin complex system. Int. J. Pharm. 28, 95–101 (1986)
Uekama, K., Fujinaga, T., Otagiri, M., Hirayama, F., Yamasaki, M.: Inclusion complexations of steroid hormones with cyclodextrins in water and in solid phase. Int. J. Pharm. 10, 1–15 (1982)
Rajagopalan, N., Chen, S.C., Chow, W.S.: A study of the inclusion complex of Amphotericin-B with γ-cyclodextrin. Int. J. Pharm. 29, 161–168 (1986)
Uekama, K., Narisawa, S., Hirayama, F., Otagiri, A.: Improvement of dissolution and absorption characteristics of benzodiazepines by cyclodextrin complexation. Int. J. Pharm. 16, 327–338 (1983)
Smulevich, G., Feis, A., Mazzi, G., Vincieri, F.F.: Inclusion complex formation of 1,8-dihydroxyanthraquinone with cyclodextrins in aqueous solution and in solid state. J. Pharm. Sci. 77, 523–526 (1988)
Xiang, T.X., Andersoon, B.D.: Inclusion complexes of purine nucleosides with cyclodextrins: II. Investigation of inclusion complex geometry and cavity microenvironment. Int. J. Pharm. 59, 45–55 (1990)
Singh, R., Bharti, N., Madan, J., Hiremath, S.N.: Characterization of cyclodextrin ınclusion complexes: a review. J. Pharm. Sci. Technol. 2, 171–183 (2010)
Ye, C.P., Ding, X.X., Li, W.Y., Mu, H., Wang, W., Feng, J.: Determination of crystalline thermodynamics and behavior of anthracene in different solvents. AIChE J. 64, 2160–2167 (2018)
Acknowledgements
We would like to thank the Kocaeli University Scientific Research Coordinator (BAP) (Project No: 2017/010), who contributed to the authors in this study, and the Gebze Technical University, Department of Chemistry, who helped to read the fluorescence lifetimes.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Sarlı, S.E., Ay, U. An Experimental Study to Synthesize and Characterize Host–Guest Encapsulation of Anthracene, and the Quenching Effects of Co and Ni. J Solution Chem 48, 1535–1546 (2019). https://doi.org/10.1007/s10953-019-00932-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-019-00932-9